| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:00 PM | Varsity | League | Normal | Away | Derby | | | | Oxford High School - OHS Wolverine Field (Turf) | 12:30 PM |
| Oxford | | |
| Wolcott | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Holy Cross | | | | Holy Cross - Alumni Field | |
| Seymour | | |
| Wilby | | |
| TUE 10/3 | 2:45 PM | Varsity | League | Normal | Away | Kennedy | | | | Woodland High School - Track | |
| Naugatuck | | |
| Woodland | | |
| THU 10/5 | 3:15 PM | Varsity | League | Normal | Away | Crosby | | | | St. Paul Catholic HS - SP Track | |
| St. Paul Catholic | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Torrington | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Watertown | | |